Water → 4-Cyclododecylbutanoic acid

HRID 37307

Reaktionsgleichung

Reaktionsgleichung von HRID 37307
[OH2:1].C(#N)C.[C:5]1([CH2:11][CH2:12][CH2:13][CH:14]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)C=CC=CC=1.I([O-])(=O)(=O)=[O:27].[Na+]>ClCCl.O.[Ru](Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[CH:14]1([CH2:13][CH2:12][CH2:11][C:5]([OH:27])=[O:1])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

8

Edukt 4

HCID 962WaterHCID 6342AcetonitrileHCID 152966211-(3-Phenylpropyl)cyclododecaneHCID 23667635Sodium periodate

Produkt 1

HCID 152966224-Cyclododecylbutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6093376Ruthenium trichloride hydrateKatalysatorHCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a flask containing 90 mL of water, 60 mL of acetonitrile and 60 mL of carbon tetrachloride is added 4.8 g (16.8 mmol) of 1-(3-phenylpropyl)cyclododecane, 50.0 g (0.25 mol) of sodium periodate and then 70 mg (0.3 mmol) of ruthenium trichloride hydrate. The reaction mixture is allowed to stir at room temperature overnight. The mixture is then taken up in dichloromethane and 1N HCl and the layers separated. The aqueous phase is washed 3 times with dichloromethane and the combined organic layers are dried over MgSO4 and the solvents evaporated. The residue is taken up in ether, filtered through Celite and the filtrate evaporated. The crude product is flash chromatographed using acidic silica gel and 30% ethyl acetate/hexanes to give 3.25 g of a white solid: NMR (CDCl3) δ 1.2-1.5 (m, 10H), 1.65 (m, 2tt), 2.35 (t, 2H, J=8 Hz).

Aufarbeitung

  1. custom1N HCl and the layers separated
  2. washThe aqueous phase is washed 3 times with dichloromethane
  3. dry with materialthe combined organic layers are dried over MgSO4
  4. customthe solvents evaporated
  5. filtrationfiltered through Celite
  6. customthe filtrate evaporated
  7. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-48835ee4c9574dbaa4113d9c6d1b2743
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420153

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